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Structural formula of the formamide molecule
Ball and stick model of formamide
Space-filling model of the formamide molecule
IUPAC name
Other names
75-12-7 YesY
ChEBI CHEBI:48431 YesY
ChEMBL ChEMBL266160 YesY
ChemSpider 693 YesY
Jmol-3D images Image
KEGG C00488 YesY
PubChem 713
Molar mass 45.04 g/mol
Appearance Colorless, oily liquid[1]
Density 1.133 g/cm3
Melting point 2 to 3 °C (36 to 37 °F; 275 to 276 K)
Boiling point 210 °C (410 °F; 483 K)
Vapor pressure 0.08 mmHg at 20 °C
Acidity (pKa) 23.5 (in DMSO)[2]
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 154 °C (309 °F; 427 K)
US health exposure limits (NIOSH):
TWA 10 ppm (15 mg/m3) [skin][1]
Related compounds
Related compounds
Carbamic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.[3]

Formamide will begin to partially decompose into carbon monoxide and ammonia at 180 °C. When heated strongly, formamide decomposes to hydrogen cyanide (HCN) and water vapor.


Historical production[edit]

In the past, formic acid was reacted with ammonia to produce ammonium formate, which yielded formamide by heating:[4]


Later a higher yielding process, aminolysis of ethyl formate, replaced this method:[5]


Modern production[edit]

The current industrial process for the manufacture of formamide involves either the reaction of carbon monoxide and ammonia:[3]


or the more important two-stage process involving the aminolysis of methyl formate (formed from carbon monoxide and methanol):


with the possibility of the resulting methanol being recycled into more methyl formate, by reaction with carbon monoxide:



Formamide is also a constituent of cryoprotectant vitrification mixtures used for cryopreservation of tissues and organs.

Formamide is also used as an RNA stabiliser in gel electrophoresis by deionizing RNA. In capillary electrophoresis, it is used for stabilizing (single) strands of denatured DNA.

Another use is to add it in sol-gel solutions in order to avoid cracking during sintering.

Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms.[6]

Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction.

Hypothetical biochemistry[edit]

Formamide has also been proposed as an alternative solvent to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth. It can be formed by the reaction of hydrogen cyanide and water, has a large dipole moment, and dissolves almost everything that will dissolve in water.[7]

RNA base creation[edit]

Formamide has been shown to create guanine at 130 °C in the presence of ultra violet light.[8]


Formamide is moderately irritating to the eyes, skin and mucous membranes.[9] Inhalation of large amounts of formamide vapor may require medical attention.[10][11] It is also a teratogen.[12] Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption.[13] Formamide should never be handled without proper safety attire including gloves and goggles. There is a small risk of decomposition into hydrogen cyanide and water.


  1. ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0295". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ F. G. Bordwell, J. E. Bartmess and J. A. Hautala (1978). "Alkyl effects on equilibrium acidities of carbon acids in protic and dipolar aprotic media and the gas phase". J. Org. Chem. 43 (16): 3095–3101. doi:10.1021/jo00410a001. 
  3. ^ a b Hohn, A. (1999). "Formamide". In Kroschwitz, Jacqueline I. Kirk-Othmer Concise Encylclopedia of Chemical Technology (4th ed.). New York: John Wiley & Sons, Inc. pp. 943–944. ISBN 978-0471419617. 
  4. ^ Lorin, M. (1864). "Preparation of Formamide by means of Formiates and Oxalates". The Chemical News and Journal of Physical Science IX: 291. Retrieved 14 June 2014. 
  5. ^ Phelps, I.K.; Deming, C.D. (1908). "The Preparation of Formamide from Ethyl Formate and Ammonium Hydroxide". The Chemical News and Journal of Physical Science. XCVII: 86–87. Retrieved 14 June 2014. 
  6. ^ Vimal K. Kamineni, Yuri M. Lvov, and Tabbetha A. Dobbins (2007). "Layer-by-Layer Nanoassembly of Polyelectrolytes Using Formamide as the Working Medium". Langmuir 23 (14): 7423–7427. doi:10.1021/la700465n. PMID 17536845. 
  7. ^ Committee On The Limits Of Organic Life In Planetary Systems (2007). The Limits of Organic Life in Planetary Systems. Washington, DC: The National Academies Press. p. 74. ISBN 0-309-66906-5. Retrieved 2012-08-29. 
  8. ^ "Origin of Life: Adding UV Light Helps Form 'Missing G' of RNA Building Blocks". Science Daily. June 14, 2010. 
  9. ^ TOXNet Formamide HSDB: Formamide
  10. ^ Warheit DB1, Kinney LA, Carakostas MC, Ross PE (1989). "Inhalation toxicity study of formamide in rats". FUNDAMENTAL AND APPLIED TOXICOLOGY 13 (4): 702–713. PMID 2620791. 
  11. ^ MSDS for formamide,
  12. ^ Lab use of formamide, University of Bath
  13. ^ [1] ECHA Formamide